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Berkshires Family Oasis with Hot Tub, Patio, Gym

All seasons family retreat in PRIME Berkshires location. Located adjacent to the famous Appalachian trail, 5 minutes from downtown Great Barrington, 2 minutes from Ski Butternut and 15 minutes from Tanglewood in Lenox. Easy access to sensational hiking, dining, lakes and museums. The home is spacious and open with 4 BR, 7 beds, a large finished basement TV & game room space and backyard patio and hot tub. A perfect spot to enjoy the spectacular beauty and unlimited activities of the Berkshires.

Quiet Cottage on the Hill — Berkshires Retreat

Quiet Cottage on the Hill — a private 5-bedroom home overlooking Haystack Mountain on a 100-acre property with private trails, in the Southfield village of New Marlborough. Private bluestone patio with wood-burning fire pit surrounded by cedar Adirondack chairs, private hot tub, kitchen with Wolf range and Sub-Zero. Comfortably hosts 6 to 8; sleeps up to 12. 5 minutes to the Southfield Store, beloved village gathering spot; 12 to Gedney Farm and the Old Inn on the Green; 25 to Great Barrington.

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Serene+Stylish Mountain Retreat

Our beautifully-designed, comfortable, much-loved townhome is great for families or friends wanting an escape to the Berkshire mountains. Located up the hill from Jiminy Peak Village Center, the home has 4 bedrooms over 3 floors, an open plan living space, updated kitchen, family room, and new deck. A short walk to the slopes in winter and use of Jiminy Peak resort pools in the summer make it a year-round destination. Book your stay and find out why once you are here, it’s so hard to leave!

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

Charming Country House with a Hot Tub

Nested in the southern Berkshire County, this private house is perfect for all seasons. It's a 15 minute drive from Great Barrington as well as skiing, swimming lakes, trails and tons of nature. Set on a secluded 2-acre lot, the house offers ample outdoor space with a hot tub that runs all year, a firepit and out door dining area. The house features an open kitchen and dining area, a spacious and well-appointed living room with a gas fireplace, kids play area, a garage with EV charging.

Lux on the River near Tanglewood w/220v EV charge

Relax with the family in this beautiful new home on the Farmington River, featuring open living spaces, a fireplace, full kitchen, two bedrooms, and a walk‑out deck to enjoy the sounds of the water. Explore nearby arts at Tanglewood, with musicians such as James Taylor, Bonnie Raitt, ++, Jacobs Pillow, and Becket, hike the Appalachian Trail, kayak on Otis Reservoir, and enjoy fall foliage or winter skiing (close by Butternut Ski Lodge) A perfect year‑round getaway for every traveler

Ski-InSki-Out Loft Lift&MT.Views

This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall.

Sweet Dreams Retreat

Romantic weekend getaway, featuring fireplaces, hot tub, swimmingpool, and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.

Spacious Lenox Farmhouse | Retreat Near Tanglewood

Welcome to Green Garden! This charming 3 bedroom, 2.5 bathroom New England farmhouse is your new favorite retreat in the Berkshires. After a day of exploring, kick back by the glow of the fire pit or relax inside. Minutes from Tanglewood and downtown Lenox, you’ll enjoy farmer’s markets, great dining, and peaceful star-filled nights. The house is kid-friendly with a Pack ’n Play, Tripp Trapp high chair, and Inglesina Fast Table.

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure ★☆ ABOUT THIS SPACE ☆★ Welcome to Jiminy Peak Slopeside Getaway, your all-season mountain retreat. Enjoy scenic views and a true ski-in/ski-out experience—just a 3-minute walk to the chair lift at Jiminy Peak. This 2-bedroom, 2-bath home sleeps up to 7 guests and offers private parking, a porch, and a deck, plus access to a heated pool, indoor/outdoor hot tub, and clubhouse.

All new mountain retreat near Great Barrington.

Kick back and relax in this calm, stylish space. Amazing restaurants, hiking and biking trails, fishing, and ski mountains just minutes away. Fully remodeled top to bottom with modern Scandinavian design and top of the line finishings. 5 min from Catamount, 10 min from Great Barrington, 15 min from Butternut, 25 min from Lime Rock. Great for families and pet friendly. Full gym, game room, and scenic privacy.